Method for marking mineral oils with amthraquinones

Details Method for marking mineral oils with amthraquinones Method for marking mineral oils with amthraquinones

1995-09-18

1997-09-02

Prior, Kimberly J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Polycyclo ring system containing anthracene configured ring...

552200, 552240, 552242, C09B 116

Patent

active

056633866

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/00673, filed Mar. 7, 1994, published as WO94/21752, Sep. 29, 1994.
The present invention relates to the use of anthraquinones of the formula Ia ##STR2## where R.sup.3 is C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by hydroxyl, cyano or phenyl and may be interrupted by from 1 to 3 ether oxygen atoms or from 1 to 3 N-(C.sub.1 -C.sub.4 -alkyl)-imino groups or is phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, (C.sub.1 -C.sub.4 -mono- or dialkylcarbamoyl)-C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.8 -mono- or dialkylsulfamoyl, where the alkyl groups may be interrupted by from 1 to 3 ether oxygen atoms, for marking mineral oils, mineral oils marked with the abovementioned anthraquinones, and dye mixtures containing an oil-soluble dye and an abovementioned anthraquinone.
The present invention furthermore relates to a method of detecting anthraquinones of the formula Ib ##STR3## R.sup.1 is hydrogen, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by cyano, or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, hydroxyl or C.sub.1 -C.sub.4 -alkoxy, and R.sup.2 is hydrogen or a radical of the formula X--R.sup.3, where X is oxygen or sulfur and R.sup.3 has the abovementioned meanings, in mineral oils by treating the latter with an aqueous alkaline medium.
EP-A-147 704 and EP-A-149 125 disclose 1,4-dihydroxyanthraquinones which have a substituted amino group in the ring position 2 as markers for mineral oils. However, it has been found that the compounds stated there have unsatisfactory performance characteristics. Thus, they exhibit, for example, insufficient stability to alkalis.
U.S. Pat. No. 3,164,449 discloses dye mixtures comprising N-substituted 1-hydroxy-4-aminoanthraquinones, suitable substituents being hexadecyl, octadecyl, octadecenyl and octadecadienyl. These dye mixtures, like the anthraquinones mentioned in GB-A-552 882, are used as dyes for dyeing mineral oils. There is no indication of the use as markers in either of these documents.
It is an object of the present invention to provide novel agents for marking mineral oils. The novel agents should be easily obtainable and readily soluble in mineral oils. Moreover, they should be capable of being detected in a simple manner. Even very small amounts of marker should be capable of being rendered visible by a strong color reaction. Finally, the marker should have good stability in the alkaline detection reaction.
We have found that this object is achieved and that the anthraquinones of the formula Ia which are defined at the outset are advantageous for marking mineral oils.
All alkyl radicals occurring in the abovementioned formulae Ia and Ib may be either straight-chain or branched.
If substituted alkyl groups occur in the abovementioned formulae Ia and Ib, they have, as a rule, 1 or 2 substituents.
If phenyl groups occur in the abovementioned formulae Ia and Ib, they have, as a rule, from 1 to 3 substituents.
R.sup.1 and R.sup.3 are each, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and originate from the alcohols obtained by the oxo synthesis, cf. Ullmanns Encyklopadie der technischen Chemie, 4th Edition, Volume 7, pages 215 to 217, and Volume 11, pages 435 and 436), tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, cyanomethyl, 2-cyanoethyl, 2- or 3-cyanopropyl, 2- or 4-cyanobutyl, 5-cyanopentyl, 6-cyanohexyl, phenyl, 2-, 3-or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-hydroxyphenyl, 2,4-dihydroxyphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl or 2,4-dimethoxyphenyl.
R.sup.3 may furthermore be, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-pro

REFERENCES:
patent: 1898953 (1933-02-01), Grossmann
patent: 3164449 (1965-01-01), Buxbaum

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